ENANTIOSELECTIVE CONSTRUCTION OF SPIRO(CYCLOPROPANE-1,4'-BICYCLO[3.3.0]OCT-1-EN-3-ONES)

被引：63

作者：

STOLLE, A

BECKER, H

SALAUN, J

DEMEIJERE, A

机构：

[1] UNIV PARIS 11,INST CHIM MOLEC ORSAY,CARBOCYCLES LAB,F-91405 ORSAY,FRANCE

[2] UNIV GOTTINGEN,INST ORGAN CHEM,D-37077 GOTTINGEN,GERMANY

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 21期

关键词：

PAUSON-KHAND REACTION; INTRAMOLECULAR; METHYLENECYCLOPROPANES; DOUBLE BOND ACTIVATION IN; SPIRO(CYCLOPROPANE-1,4'-BICYCLO[3.3.0]OCT-1-EN-3-ONES) ENANTIOMERICALLY PURE COMPOUNDS; STEREOSELECTION;

D O I：

10.1016/S0040-4039(00)73225-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Intramolecular Pauson-Khand reactions of 1,6-enynes 3a-c with a methylenecyclopropane terminator and a chiral acetal moiety adjacent to the triple bond gave spiro{cyclopropane-1,4'-bicyclo[3.3.0]oct-1-en-3-ones} 5a-c in good yields with a diastereoselectivity of up to 6.4:1. The major diastereomer of 5b was converted to enantiomerically pure bicyclo[3.3.0]octane-3,8-dione 8, which showed a negative peak at 287 nm in the CD curve, consistent with an assumed (5R) configuration.

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页码：3521 / 3524

页数：4

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